Ethanol → 2-(2-Methoxyphenyl)-2-oxoacetaldehyde

HRID 653035Notes

Reaction equation

HRID 653035 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:11])[CH3:10].C([OH:14])C>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([CH:10]=[O:14])=[O:11]

Participants

3

Reactant 2

HCID 702EthanolHCID 684812'-Methoxyacetophenone

Product 1

HCID 75786512-(2-Methoxyphenyl)-2-oxoacetaldehyde

Procedure

SeO2 (12.4 g., 0.112 mol) was dissolved in 75 ml. of 95% ethanol by warming to 55°. o-Methoxyacetophenone (15.3 g., 0.102 mol) was added in one portion and the mixture refluxed 21 hours. The reaction mixture was treated with activated carbon, filtered over diatomaceous earth, and the filtrate stripped to yield to an oil, 23.2 g. The latter was distilled to yield purified title product, 8.4 g., bp 94°-96°/0.5 mm, which solidified on cooling.

Workup

  1. temperaturethe mixture refluxed 21 hours
  2. additionThe reaction mixture was treated with activated carbon
  3. filtrationfiltered over diatomaceous earth
  4. customto yield to an oil, 23.2 g
  5. distillationThe latter was distilled
  6. customto yield
  7. custompurified title product, 8.4 g
  8. temperatureon cooling

Sources & evidence

ORD record
ord-f3d933460c0e42d6817583887b7f4206
Source dataset
uspto-grants-1987_06
Patent number
US04675186

Reaction notes

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